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Method for synthesizing 6-substituent-3-hydroxy-4-methoxybenxaldchyde

A technology of methoxybenzaldehyde and dimethoxybenzaldehyde, which is applied in the field of synthesis of organic compounds, can solve problems such as poor product color, difficulty in meeting commercial production needs, and synthetic methods that have not been adopted. The effect of low cost, reduced production cost, and simple synthesis process

Inactive Publication Date: 2005-10-26
ZHEJIANG UNIV
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

Among them, 6-bromo-3-hydroxyl-4-methoxybenzaldehyde is an important intermediate for the chemical synthesis of galantamine, and its existing synthetic methods are rarely seen in reports; and the product has poor color and luster, which is difficult to meet commercialization The production needs of (Bulavka V.N., Tolkachev O.N., Shchavlinskii.A.N.Khim.-Farm.Zh.(Russian), 1990, 24(5):59-60; Bernhard Küenburg.Laszlo Czollner, Johannes Frhlich, Ulrich Jordis.Development of a Pilot Scale Process for the Anti-Alzheimer Drug(-)-Galanthamine Using Large-ScalePhenolic Oxidative Coupling and Crystallisation-Induced Chiral Conversion[J].Organic Process Research&Development, 1999, 3:425-431.)
At present, the synthetic method of 6-substituting group-3-hydroxyl-4-methoxybenzaldehyde has not yet been seen and adopted

Method used

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  • Method for synthesizing 6-substituent-3-hydroxy-4-methoxybenxaldchyde
  • Method for synthesizing 6-substituent-3-hydroxy-4-methoxybenxaldchyde

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Experimental program
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Effect test

Embodiment 1

[0018] Embodiment 1: the synthesis of 6-bromo-3-hydroxyl-4-methoxybenzaldehyde

[0019] (1) Demethylation reaction:

[0020] Dissolve 6-bromo-3,4-dimethoxybenzaldehyde (24.5g, 0.1mol) in 200mL of concentrated sulfuric acid with a concentration of 96%, and add DL-methionine in batches for 30min under stirring at 20-25°C (17.9g, 0.12mol), heated up to 90-95°C, and reacted for 3h. (At this time, the reaction liquid was taken for HPLC analysis, and the content of 6-bromo-3,4-dimethoxybenzaldehyde was <1%). Under stirring, the reaction solution was poured into 1500mL of ice water in a thin stream while it was hot, filtered (retain the filtrate for the third step experiment), and the filter cake was washed with 3×10mL saturated aqueous sodium chloride solution to obtain 6-bromo-3-hydroxyl-4 - crude product of methoxybenzaldehyde.

[0021] (2) Purification:

[0022] Dissolve the crude product obtained in the above operation with 100mL of 40% aqueous sodium hydroxide solution, fil...

Embodiment 2

[0025] Embodiment 2: the synthesis of 6-nitro-3-hydroxyl-4-methoxybenzaldehyde

[0026] (1) Demethylation reaction:

[0027] Dissolve 6-nitro-3,4-dimethoxybenzaldehyde (21.1g, 0.1mol) in 220mL of 97% concentrated sulfuric acid, add DL-methionine in batches for 30min under stirring at 20-25°C (20.9g, 0.14mol), heated up to 60-65°C, and reacted for 6h. (At this time, the reaction liquid was analyzed by HPLC, and the content of 6-nitro-3,4-dimethoxybenzaldehyde was <1%). Under stirring, the reaction solution was poured into 1650mL of ice water in a thin stream while it was hot, filtered (the filtrate was retained for the third step experiment), and the filter cake was washed with 3×10mL saturated aqueous sodium chloride solution to obtain 6-nitro-3-hydroxy- Crude 4-methoxybenzaldehyde.

[0028] (2) Purification:

[0029] Dissolve the crude product obtained in the above operations with 80 mL of 40% aqueous sodium hydroxide solution, filter, adjust the pH value of the filtrate ...

Embodiment 3

[0032] Embodiment 3: the synthesis of 6-amino 3-hydroxyl-4-methoxybenzaldehyde

[0033] (1) Demethylation reaction:

[0034] 6-Amino-3,4-dimethoxybenzaldehyde (18.1 g, 0.1 mol) was dissolved in 250 mL of 98% concentrated sulfuric acid, and DL-methionine ( 17.9g, 0.12mol), heated up to 70-75°C, and reacted for 4h. (At this time, the reaction liquid was analyzed by HPLC, and the content of 2-amino-3,4-dimethoxybenzaldehyde was <1%). Under stirring, pour the reaction solution into 2000mL ice water in a thin stream while it is hot, adjust the pH value to 7-8 with 40% sodium hydroxide solution, filter (retain the filtrate for the third step experiment), filter the cake with 3×10mL saturated chlorine Washing with aqueous sodium chloride solution gave crude 6-amino-3-hydroxy-4-methoxybenzaldehyde.

[0035] (2) Purification:

[0036] Dissolve the crude product obtained by the above operation with 90 mL of 40% aqueous sodium hydroxide solution, filter, adjust the pH value of the fi...

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Abstract

The present invention discloses a synthesis method of 6-substituent-3-hydroxy-4-methoxybenzaldehyde. Said method includes the following steps: (1). demethylation; under the action of concentrated sulfuric acid making 6-substituent-3,4-dimethoxybenzaldehyde and DL-methionine be reacted, after the reaction is completed, diluting and filtering to obtain filtrate and filter cake, washing filter cake to obtain 6-substituent-3-hydroxy-4-methoxybenzaldehyde crude product; (2). purification: using alkaline solution to dissolve the above-mentioned crude product, filtering, using acidic solution to regulate pH value of obtained filtrate to acidity, filtering, washing, drying so as to obtain 6-substituent-3-hydroxy 4-methoxybenzaldehyde; and (3) recovering DL-methionine.

Description

technical field [0001] The invention relates to a synthesis method of a class of organic compounds, in particular to a synthesis method of 6-substituent-3-hydroxyl-4-methoxybenzaldehyde. Background technique [0002] [0003] Wherein: X=bromine, chlorine, nitro, amino, hydroxyl, alkoxy (wherein the alkyl is an alkyl less than five carbon atoms) and the like. [0004] S-1 [0005] The 6-substituent-3-hydroxy-4-methoxybenzaldehyde with the molecular formula shown in S-1 is an important fine chemical product and pharmaceutical intermediate. Among them, 6-bromo-3-hydroxyl-4-methoxybenzaldehyde is an important intermediate for the chemical synthesis of galantamine, and its existing synthetic methods are rarely seen in reports; and the product has poor color and luster, which is difficult to meet commercialization The production needs of (Bulavka V.N., Tolkachev O.N., Shchavlinskii.A.N.Khim.-Farm.Zh.(Russian), 1990, 24(5):59-60; Bernhard Küenburg.L...

Claims

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Application Information

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IPC IPC(8): C07C47/575
Inventor 陈新志刘涛
Owner ZHEJIANG UNIV
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